Alkynes and methods of reacting alkynes with 1,3-dipole-functional compounds

Abstract

1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.

What is claimed is: 
     
       1. A dibenzocyclooctyne having the formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 each R 1  and R 2  is hydrogen; 
 X represents CHOR 3 ; and 
 R 3  represents an organic group comprising a biotin fragment. 
 
     
     
       2. A dibenzocyclooctyne having the formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 each R 1  and R 2  is hydrogen; 
 X represents CHOR 3 ; and 
 R 3  represents an organic group comprising a covalently bound organic dye. 
 
     
     
       3. A dibenzocyclooctyne having the formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 each R 1  is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group; 
 each R 2  is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group; 
 X represents C═N—OR 3 , C═N—NR 3 R 4 , CHOR 3 , or CHNHR 3 ; 
 R 3  represents an organic group attached to a nanoparticle; and 
 R 4  represents hydrogen or an organic group. 
 
     
     
       4. A method of preparing a heterocyclic compound, the method comprising:
 combining at least one azide-functional compound with at least one dibenzocyclooctyne according to  claim 3 ; and 
 allowing the at least one azide-functional compound and the at least one alkyne to react under conditions effective to form the heterocyclic compound. 
 
     
     
       5. An alkyne of the formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 each R 1  and R 2  is hydrogen; 
 X represents CHOR 3 ; and 
 R 3  represents an organic group.